Organic compound, light-emitting element, and display panel
By using organic compounds with heterocyclic and amine groups, the material resonance effect in OLED devices was enhanced, solving the problems of luminous efficiency and stability, improving luminous efficiency and extending luminous lifetime.
Patent Information
- Authority / Receiving Office
- CN · China
- Patent Type
- Patents(China)
- Current Assignee / Owner
- Filing Date
- 2022-12-12
- Publication Date
- 2026-04-07
Smart Images

Figure CN116120352B_ABST
Abstract
Description
TECHNICAL FIELD
[0001] The present application relates to the field of display, in particular to an organic compound, a light-emitting element and a display panel. BACKGROUND
[0002] At present, the organic electroluminescent element generally has a positive electrode, a negative electrode and an organic layer between the two, which converts electrical energy into light energy by using the organic matter of the organic layer, so as to realize organic electroluminescence. In order to improve the luminous efficiency and service life of the organic electroluminescent element, the organic layer is often multilayer, and the organic matter of each layer is different. Specifically, the organic layer mainly includes a hole injection layer, a hole transport layer, a light-emitting layer, an electron transport layer, an electron injection layer and the like. A voltage is applied between the positive electrode and the negative electrode of the organic electroluminescent element, the positive electrode injects holes into the organic layer, and the negative electrode injects electrons into the organic layer. The injected holes and electrons meet to form excitons, and the excitons emit light when they transition back to the ground state, thereby realizing the light emission of the organic electroluminescent element. The organic electroluminescent element has the characteristics of self-luminous, high brightness, high efficiency, low voltage driving, wide viewing angle, high contrast and high response, etc. Therefore, the organic electroluminescent device has a wide application prospect.
[0003] Correspondingly, the material development of organic light emitting diode (OLED) has also been widely concerned due to its advantages such as diversity in synthesis, simple composition and process, etc. At the same time, in order to improve the luminous efficiency of the organic electroluminescent element, various energy transfer and conversion mechanism material systems have been tried, but the luminous efficiency, stability and life performance of the light-emitting material applied to the OLED element are still low, which limits the performance improvement of the OLED element.
[0004] Therefore, there is an urgent need for an organic compound, a light-emitting element and a display panel to solve the above technical problems. SUMMARY
[0005] The present application provides an organic compound, a light-emitting element and a display panel, which can alleviate the technical problem that the luminous efficiency, stability and life performance of the light-emitting material applied to the OLED element are low, which leads to the difficulty in improving the performance of the OLED element.
[0006] The present application provides an organic compound, which has a structure as shown in general formula (1):
[0007]
[0008] wherein Z is selected from CR1R2, NR3, O or S;
[0009] X is selected from O or NR4;
[0010] R1-R4are each independently selected at each occurrence from substituted or unsubstituted alkyl of 1-4 carbon atoms, substituted or unsubstituted aromatic group of 6-29 carbon atoms, substituted or unsubstituted heteroaromatic group of 26-36 carbon atoms;
[0011] R1, R2are connected to each other to form a ring or not;
[0012] Ar1is selected from H, D, substituted or unsubstituted alkyl of 1-6 carbon atoms, substituted or unsubstituted aromatic group of 6-20 carbon atoms, substituted or unsubstituted heteroaromatic group of 12-20 carbon atoms;
[0013] Ar2-Ar3are each independently selected from methyl, substituted or unsubstituted aromatic group of 7-18 carbon atoms, substituted or unsubstituted heteroaromatic group of 12-16 carbon atoms;
[0014] Ar4-Ar6are each independently selected from substituted or unsubstituted aromatic group of 6-31 carbon atoms, substituted or unsubstituted heteroaromatic group of 6-26 carbon atoms.
[0015] Preferably, the organic compound has a structure as shown in any one of general formula (2) to general formula (11):
[0016]
[0017]
[0018] Preferably, the organic compound has a structure as shown in general formula (12):
[0019]
[0020] wherein Y is selected from CR5R6, NR7, O or S;
[0021] R5-R7are each independently selected at each occurrence from substituted or unsubstituted methyl, substituted or unsubstituted aromatic group of 6-10 carbon atoms;
[0022] R5, R6are connected to each other to form a ring or not;
[0023] Ar7-Ar8are each independently selected from substituted or unsubstituted aromatic group of 6-10 carbon atoms;
[0024] Ar9is selected from substituted or unsubstituted phenyl.
[0025] Preferably, R5-R7are each independently selected at each occurrence from methyl, substituted or unsubstituted phenyl;
[0026] Ar7-Ar8are each independently selected from the group consisting of methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl;
[0027] Ar9is independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl.
[0028] Preferably, the organic compound has a structure as shown in general formula (13):
[0029]
[0030] wherein A is CR9R 10 , NR 11 , O or S;
[0031] n is an integer from 0 to 4;
[0032] R8-R 11 are each independently selected at each occurrence from the group consisting of substituted or unsubstituted alkyl of 1 to 4 carbon atoms, substituted or unsubstituted aromatic group of 6 to 10 carbon atoms;
[0033] when n is equal to 0, R9, R 10 are linked to each other to form or not to form a ring, and when n is greater than or equal to 1, R8and R9and / or R 10 are linked to each other to form or not to form a ring.
[0034] Preferably, the organic compound has a structure as shown in general formula (14):
[0035]
[0036] wherein Ar 10 -Ar 11 are each independently selected from the group consisting of methyl, substituted or unsubstituted aromatic group of 6 to 18 carbon atoms, substituted or unsubstituted heteroaromatic group of 5 to 13 carbon atoms;
[0037] Ar 12 is selected from the group consisting of substituted or unsubstituted phenyl.
[0038] Preferably, Ar 10 -Ar 11each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl.
[0039] Preferably, Ar1is selected from the group consisting of H, D, methyl, isopropyl, t-butyl, t-amyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl, substituted or unsubstituted amine;
[0040] Ar2-Ar3are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl;
[0041] Ar4-Ar6are each independently selected from the group consisting of substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorene, substituted or unsubstituted carbazolyl;
[0042] R1-R4are each independently selected from the group consisting of methyl, substituted or unsubstituted phenyl.
[0043] Preferably, the organic compound is selected from the group consisting of:
[0044]
[0045]
[0046]
[0047]
[0048]
[0049]
[0050]
[0051]
[0052] The present application also provides a light-emitting element comprising:
[0053] a pair of electrodes including a first electrode and a second electrode;
[0054] an organic functional layer between the first electrode and the second electrode;
[0055] The material of the organic functional layer comprises one or more than one of the organic compound according to any one of the above.
[0056] Preferably, the organic functional layer comprises at least a light-emitting layer, and the light-emitting layer comprises a host material and a guest material, and the guest material is one or more than one of the organic compound according to any one of the above.
[0057] The present application also provides a display panel comprising the light-emitting element according to any one of the above.
[0058] The present application enhances the resonance effect of the material applied in the light-emitting element by using the organic compound containing amine group, and the organic compound contains both heterocycle and amine group, improves the material performance, increases the light-emitting efficiency of the light-emitting element and prolongs the light-emitting life of the light-emitting element. BRIEF DESCRIPTION OF DRAWINGS
[0059] In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings needed to be used in the embodiments will be briefly introduced as follows. Obviously, the drawings in the following description are only some embodiments of the present application, and other drawings can be obtained by those skilled in the art without any creative effort based on these drawings.
[0060] Figure 1 is a first structure schematic diagram of the light-emitting element provided by the embodiments of the present application;
[0061] Figure 2 is a second structure schematic diagram of the light-emitting element provided by the embodiments of the present application. DETAILED DESCRIPTION
[0062] The technical solutions in the embodiments of the present application will be described clearly and completely below with reference to the drawings in the embodiments of the present application. Obviously, the described embodiments are only part of the embodiments of the present application, rather than all the embodiments of the present application. Based on the embodiments in the present application, all the other embodiments obtained by a person of ordinary skill in the art without creative work fall within the protection scope of the present application. In addition, it should be understood that the specific implementation described herein is only used for illustrating and explaining the present application, and is not used for limiting the present application. In the present application, the orientation words such as "upper" and "lower" generally refer to the upper and lower in the actual use or working state of the device, and specifically refer to the direction of the drawing in the drawings. The "inner" and "outer" refer to the contour of the device. In the present application, "optionally", "optional" and "optionally" mean that it can or can not be present, that is, it is selected from any one of the two parallel schemes of "yes" or "no". If there are multiple "optionally" in a technical solution, if there is no special description, and there is no contradictory relationship or mutual restriction, each "optionally" is independent. In the present application, the technical features described in an open manner include closed technical solutions composed of listed features, and also include open technical solutions containing listed features.
[0063] In the present application, the aromatic group, aromatic, aromatic ring system have the same meaning and can be interchangeable.
[0064] In the present application, the heteroaromatic group, heteroaromatic, heteroaromatic ring system have the same meaning and can be interchangeable.
[0065] In the present application, "substituted" means that the hydrogen atom in the substituent is replaced by the substituent.
[0066] In the present application, the same substituent can be independently selected from different groups when it appears multiple times. For example, if the general formula contains multiple R, R can be independently selected from different groups.
[0067] In the present application, "substituted or unsubstituted" means that the defined group can be substituted or unsubstituted. When the defined group is substituted, it is understood that the defined group can be substituted with one or more substituents R selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group having 1 to 20 carbon atoms, a heterocyclic group having 3 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, -NR'R", a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogen carboxyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups can be further substituted with an acceptable substituent in the art; it is understood that R' and R" in -NR'R" are each independently selected from, but not limited to, H, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group having 1 to 10 carbon atoms, a heterocyclic group having 3 to 20 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms. Preferably, R is selected from, but not limited to, a deuterium atom, a cyano group, an isocyano group, a nitro group, or a halogen, an alkyl group having 1 to 10 carbon atoms, a heterocyclic group having 3 to 10 ring atoms, an aromatic group having 6 to 20 ring atoms, a heteroaromatic group having 5 to 20 ring atoms, a silyl group, a carbonyl group, an alkoxycarbonyl group, an aryloxycarbonyl group, a carbamoyl group, a halogen carboxyl group, a formyl group, an isocyanate group, a thiocyanate group, an isothiocyanate group, a hydroxyl group, a trifluoromethyl group, and the above groups can be further substituted with an acceptable substituent in the art.
[0068] In the present application, "ring atom number" means the number of atoms constituting a ring itself in a structural compound obtained by bonding atoms into a ring (e.g., a monocyclic compound, a fused ring compound, a crosslinked compound, a carbocyclic compound, a heterocyclic compound). When the ring is substituted with a substituent, the atoms included in the substituent are not included in the ring-forming atoms. The same applies to the "ring atom number" described below, unless otherwise specified. For example, the ring atom number of a benzene ring is 6, the ring atom number of a naphthalene ring is 10, and the ring atom number of a thiophene group is 5.
[0069] In the present invention, "aryl or aromatic group" refers to aromatic hydrocarbon group derived from removing one hydrogen atom from aromatic ring compound, which can be monocyclic aryl, or fused ring aryl, or polycyclic aryl, and at least one of the rings in the polycyclic ring is aromatic ring system. For example, "substituted or unsubstituted aryl having 6 to 40 ring atoms" refers to aryl having 6 to 40 ring atoms, preferably substituted or unsubstituted aryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted aryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted aryl having 6 to 14 ring atoms, and the aryl is optionally further substituted; suitable examples include, but are not limited to: phenyl, biphenyl, terphenyl, naphthyl, anthryl, phenanthryl, fluoranthenyl, pyrenyl, chrysenyl, tetracenyl, pyrenyl, pyrenyl, perylenyl, naphthacenyl, acenaphthyl, and derivatives thereof. It can be understood that multiple aryl groups can also be interrupted by short non-aromatic units (e.g. <10% non-H atoms such as C, N or O atoms), in particular acenaphthene, fluorene, or 9,9-dialkylfluorene, triarylamine, diaryl ether systems should also be included in the definition of aryl.
[0070] In the present invention, "heteroaryl or heteroaromatic group" refers to at least one carbon atom in aryl being replaced by a non-carbon atom, which can be N atom, O atom, S atom, etc. For example, "substituted or unsubstituted heteroaryl having 5 to 40 ring atoms" refers to heteroaryl having 5 to 40 ring atoms, preferably substituted or unsubstituted heteroaryl having 6 to 30 ring atoms, more preferably substituted or unsubstituted heteroaryl having 6 to 18 ring atoms, particularly preferably substituted or unsubstituted heteroaryl having 6 to 14 ring atoms, and the heteroaryl is optionally further substituted; suitable examples include, but are not limited to: thienyl, furanyl, pyrrolyl, imidazolyl, oxadiazolyl, triazolyl, imidazolyl, pyridyl, bipyridyl, pyrimidyl, triazinyl, acridinyl, pyridazinyl, pyrazinyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, benzothienyl, benzofuranyl, indolyl, pyrroloimidazolyl, pyrrolopyrrolyl, thienopyrrolyl, thienothienyl, furanopyrrolyl, furanofuranyl, thienofuranyl, benzisoxazolyl, benzisothiazolyl, benzimidazolyl, perylenyl, phenanthridinyl, perimidinyl, quinazolinonyl, dibenzothiophenyl, dibenzofuranyl, carbazolyl, and derivatives thereof.
[0071] In the present invention, "amino group" refers to derivative of amine, having the structural feature of formula -NR'R", and R' and R" have the same meaning as described above.
[0072] In this invention, an asterisk (*) connected to a single bond indicates a linking or fusion site; when no linking site is specified in the group, any linkable site in the group is selected as the linking site; when the same group contains multiple substituents with the same symbol, the substituents can be the same or different from each other, for example... The six R's on the benzene ring can be the same or different from each other; the single bonds connecting the substituents extend through the corresponding ring, indicating that the substituent can be attached to any position on the ring, for example... R is attached to any substituted site on the benzene ring.
[0073] Currently, due to the low luminous efficiency, stability, and lifespan of the luminescent materials used in OLED devices, there is a problem that it is difficult to improve the performance of OLED devices.
[0074] This invention provides an organic compound having a structure as shown in general formula (1):
[0075]
[0076] Z is selected from CR1R2, NR3, O, or S;
[0077] X is selected from O or NR4;
[0078] Each time R1-R4 appears, they are independently selected from alkyl groups with 1-20 carbon atoms that are substituted or unsubstituted, aromatic groups with 6-30 carbon atoms that are substituted or unsubstituted, and heteroaromatic groups with 5-36 carbon atoms that are substituted or unsubstituted.
[0079] R1 and R2 may be connected to each other to form a loop or not;
[0080] Ar1 is selected from H, D, alkyl groups with 1-20 carbon atoms (substituted or unsubstituted), aromatic groups with 6-30 carbon atoms (substituted or unsubstituted), and heteroaromatic groups with 5-30 carbon atoms (substituted or unsubstituted).
[0081] Ar2-Ar3 are each independently selected from alkyl groups of 1-20 carbon atoms that are substituted or unsubstituted, aromatic groups of 6-30 carbon atoms that are substituted or unsubstituted, and heteroaromatic groups of 5-30 carbon atoms that are substituted or unsubstituted.
[0082] Ar4-Ar6 are each independently selected from aromatic groups of 6-31 carbon atoms (substituted or unsubstituted) and heteroaromatic groups of 5-30 carbon atoms (substituted or unsubstituted).
[0083] This invention enhances the resonance effect of materials used in light-emitting elements by using an amine-containing organic compound that simultaneously contains heterocycles and amine groups, thereby improving material properties, increasing the luminous efficiency of the light-emitting element, and extending the luminous lifespan of the light-emitting element.
[0084] In some embodiments, the organic compound has a structure as shown in any of general formulas (2) to (11):
[0085]
[0086] In some embodiments, Z is preferably from CR1R2, O, or S, more preferably from O or S.
[0087] In some embodiments, X is preferably NR4.
[0088] In some embodiments, the organic compound has a structure as shown in general formula (12):
[0089]
[0090] In some embodiments, Y is selected from CR5R6, NR7, O, or S.
[0091] In some embodiments, each of R5-R7 is independently selected from alkyl groups of 1-20 carbon atoms (substituted or unsubstituted), aromatic groups of 6-30 carbon atoms (substituted or unsubstituted), and heteroaromatic groups of 5-30 carbon atoms (substituted or unsubstituted); each of R5-R7 is preferably independently selected from alkyl groups of 1-12 carbon atoms (substituted or unsubstituted), aromatic groups of 6-20 carbon atoms (substituted or unsubstituted), or heteroaromatic groups of 5-20 carbon atoms (substituted or unsubstituted). Aromatic group; each of R5-R7 is independently preferred from an alkyl group of 1-8 carbon atoms (substituted or unsubstituted), an aromatic group of 6-15 carbon atoms (substituted or unsubstituted), or a heteroaromatic group of 5-15 carbon atoms (substituted or unsubstituted); each of R5-R7 is independently selected from a methyl group (substituted or unsubstituted) or an aromatic group of 6-10 carbon atoms (substituted or unsubstituted); each of R5-R7 is independently preferred from a methyl group or a phenyl group (substituted or unsubstituted).
[0092] In some embodiments, R5 and R6 may be connected to each other in a ring or not.
[0093] In some embodiments, Ar7-Ar8 are each independently selected from alkyl groups of 1-12 carbon atoms (substituted or unsubstituted), aromatic groups of 6-20 carbon atoms (substituted or unsubstituted), or heteroaromatic groups of 5-20 carbon atoms (substituted or unsubstituted); Ar7-Ar8 are each independently preferably selected from alkyl groups of 1-8 carbon atoms (substituted or unsubstituted), aromatic groups of 6-15 carbon atoms (substituted or unsubstituted), or heteroaromatic groups of 5-15 carbon atoms (substituted or unsubstituted); A r7-Ar8 are each independently and further preferably selected from aromatic groups of 6-10 carbon atoms or substituted or unsubstituted heteroaromatic groups of 5-10 carbon atoms; Ar7-Ar8 are each independently and further selected from methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl.
[0094] In some embodiments, Ar9 is independently preferred to be an aromatic group of 6-20 carbon atoms, substituted or unsubstituted, or a heteroaromatic group of 5-20 carbon atoms, substituted or unsubstituted; Ar9 is independently preferred to be an aromatic group of 6-15 carbon atoms, substituted or unsubstituted, or a heteroaromatic group of 5-15 carbon atoms, substituted or unsubstituted; Ar9 is independently preferred to be an aromatic group of 6-10 carbon atoms, substituted or unsubstituted, or a heteroaromatic group of 5-10 carbon atoms, substituted or unsubstituted; Ar9 is independently preferred to be a phenyl group, a naphthyl group, a triphenylene group, a dibenzofuran, a dibenzothiophene, a fluorenyl group, or a carbazoyl group, substituted or unsubstituted.
[0095] In some embodiments, the organic compound has a structure as shown in general formula (13):
[0096]
[0097] In some embodiments, A is denoted as CR9R 10 NR 11 , O or S;
[0098] In some embodiments, n is represented as an integer from 0 to 4, such as 0, 1, 2, 3, 4.
[0099] In some embodiments, R8-R 11 Each time it appears, it is independently selected from alkyl groups of 1-20 carbon atoms (substituted or unsubstituted), aromatic groups of 6-30 carbon atoms (substituted or unsubstituted), and heteroaromatic groups of 5-30 carbon atoms (substituted or unsubstituted); R8-R 11Each time it appears, it is independently preferred to have an alkyl group of 1-4 carbon atoms that is substituted or unsubstituted, an aromatic group of 6-30 carbon atoms that is substituted or unsubstituted, or a heteroaromatic group of 5-30 carbon atoms that is substituted or unsubstituted; R8-R 11 Each time it appears, it is independently selected from alkyl groups of 1-4 carbon atoms (substituted or unsubstituted) and aromatic groups of 6-10 carbon atoms (substituted or unsubstituted); R8-R 11 Each time it appears, it is independently preferred from methyl, tert-butyl, substituted or unsubstituted phenyl, wherein the substituted phenyl is preferably a tert-butyl substituted phenyl.
[0100] When n equals 0, R9, R 10 Interconnected to form loops or not, when n is greater than or equal to 1, R8 and R9 and / or R 10 They can be interconnected to form a cycle or not; that is, when n is greater than or equal to 1, R8, R9, R... 10 The three can form loops in pairs, form loops together, or not form loops.
[0101] In some embodiments, the organic compound has a structure as shown in general formula (14):
[0102]
[0103] In some embodiments, Ar 10 -Ar 11 Each is independently preferred from alkyl groups of 1-12 carbon atoms (substituted or unsubstituted), aromatic groups of 6-24 carbon atoms (substituted or unsubstituted), and heteroaromatic groups of 5-24 carbon atoms (substituted or unsubstituted); Ar 10 -Ar 11 Each is independently preferred from alkyl groups of 1-12 carbon atoms (substituted or unsubstituted), aromatic groups of 6-20 carbon atoms (substituted or unsubstituted), and heteroaromatic groups of 5-20 carbon atoms (substituted or unsubstituted); Ar 10 -Ar 11 Each is independently preferred to be an alkyl group of 1-8 carbon atoms (substituted or unsubstituted), an aromatic group of 6-15 carbon atoms (substituted or unsubstituted), or a heteroaromatic group of 5-15 carbon atoms (substituted or unsubstituted); Ar 10 -Ar 11 Each group is independently selected from methyl, substituted or unsubstituted aromatic groups of 6-18 carbon atoms, and substituted or unsubstituted heteroaromatic groups of 5-13 carbon atoms; Ar 10 -Ar 11Each of the following is independently selected from methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorenyl, and substituted or unsubstituted carbazolyl.
[0104] In some embodiments, Ar 12 Selected from substituted or unsubstituted phenyl groups.
[0105] In the above embodiments, each time R1-R4 appears, it is independently preferred to be an alkyl group of 1-4 carbon atoms that is substituted or unsubstituted, an aromatic group of 6-30 carbon atoms that is substituted or unsubstituted, or a heteroaromatic group of 5-30 carbon atoms that is substituted or unsubstituted; each time R1-R4 appears, it is independently preferred to be an alkyl group of 1-4 carbon atoms that is substituted or unsubstituted, an aromatic group of 6-29 carbon atoms that is substituted or unsubstituted, or a heteroaromatic group of 26-36 .... Alkyl groups of 1-12 carbon atoms, substituted or unsubstituted, aromatic groups of 6-15 carbon atoms, substituted or unsubstituted, heteroaromatic groups of 5-15 carbon atoms, substituted or unsubstituted; each time R4 appears, it is independently further preferred from methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazole; each time R1-R4 appears, it is independently further preferred from methyl, substituted or unsubstituted phenyl.
[0106] In the above embodiments, Ar1 is preferably derived from H, D, alkyl groups of 1-5 carbon atoms (substituted or unsubstituted), aromatic groups of 6-30 carbon atoms (substituted or unsubstituted), or heteroaromatic groups of 5-30 carbon atoms (substituted or unsubstituted); Ar1 is preferably derived from H, D, alkyl groups of 1-6 carbon atoms (substituted or unsubstituted), aromatic groups of 6-20 carbon atoms (substituted or unsubstituted), or heteroaromatic groups of 12-20 carbon atoms (substituted or unsubstituted); Ar1 is preferably derived from H, D, alkyl groups of 1-12 carbon atoms (substituted or unsubstituted), or aromatic groups of 6-20 carbon atoms (substituted or unsubstituted). Ar1 is preferably derived from H, D, alkyl groups of 1-8 carbon atoms, aromatic groups of 6-15 carbon atoms, or heteroaromatic groups of 5-15 carbon atoms, whether substituted or unsubstituted; Ar1 is further preferably derived from H, D, methyl, isopropyl, tert-butyl, tert-amyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazole, or substituted or unsubstituted amino.
[0107] In the above embodiments, Ar2-Ar3 are each independently preferred to be composed of a substituted or unsubstituted methyl group, a substituted or unsubstituted aromatic group of 6-30 carbon atoms, or a substituted or unsubstituted heteroaromatic group of 5-30 carbon atoms; Ar2-Ar3 are each independently preferred to be composed of a substituted or unsubstituted methyl group, a substituted or unsubstituted aromatic group of 7-18 carbon atoms, or a substituted or unsubstituted heteroaromatic group of 12-16 carbon atoms; Ar2-Ar3 are each independently preferred to be composed of a substituted or unsubstituted alkyl group of 1-12 carbon atoms, a substituted or unsubstituted aromatic group of 6-20 carbon atoms, or a substituted or unsubstituted alkyl group of 1-12 carbon atoms, or a substituted or unsubstituted aromatic group of 6-20 carbon atoms. The substituted heteroaromatic group of 5-20 carbon atoms; Ar2-Ar3 are each independently preferred from substituted or unsubstituted alkyl groups of 1-8 carbon atoms, substituted or unsubstituted aromatic groups of 6-15 carbon atoms, substituted or unsubstituted heteroaromatic groups of 5-15 carbon atoms; Ar2-Ar3 are each independently further preferred from methyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted triphenylene, substituted or unsubstituted dibenzofuran, substituted or unsubstituted dibenzothiophene, substituted or unsubstituted fluorenyl, substituted or unsubstituted carbazolyl.
[0108] In the above embodiments, Ar4-Ar6 are each independently preferred to have an aromatic group of 6-31 carbon atoms that is self-substituted or unsubstituted, or a heteroaromatic group of 6-26 carbon atoms that is substituted or unsubstituted; Ar4-Ar6 are each independently preferred to have an aromatic group of 6-20 carbon atoms that is self-substituted or unsubstituted, or a heteroaromatic group of 5-20 carbon atoms that is substituted or unsubstituted; Ar4-Ar6 are each independently preferred to have an aromatic group of 6-15 carbon atoms that is self-substituted or unsubstituted, or a heteroaromatic group of 5-15 carbon atoms that is substituted or unsubstituted; Ar4-Ar6 are each independently more preferably to have a self-substituted or unsubstituted phenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted triphenylene group, a substituted or unsubstituted dibenzofuran group, a substituted or unsubstituted dibenzothiophene group, a substituted or unsubstituted fluorenyl group, or a substituted or unsubstituted carbazole group.
[0109] In some embodiments, the organic compound is selected from the following compounds:
[0110]
[0111]
[0112]
[0113]
[0114]
[0115]
[0116]
[0117]
[0118] The amine-containing organic compounds provided in this invention have both heterocyclic and amine groups, which enhance the resonance effect of materials applied to light-emitting elements, improve material properties, increase the luminous efficiency of light-emitting elements, and extend the luminous lifespan of light-emitting elements.
[0119] Please see Figure 1 as well as Figure 2 The present invention also provides a light-emitting element, the light-emitting element comprising: a pair of electrodes, including a first electrode 101 and a second electrode 102; an organic functional layer 103 located between the first electrode 101 and the second electrode 102; wherein the material of the organic functional layer 103 includes one or more organic compounds as described above. The first electrode 101 may be an anode, and the second electrode 102 may be a cathode.
[0120] In some embodiments, the light-emitting element can be an organic light-emitting diode, an organic photovoltaic cell, an organic light-emitting cell, an organic field-effect transistor, an organic light-emitting field-effect transistor, an organic laser, an organic spintronic device, an organic sensor, and an organic plasmon emitting diode, etc., preferably an organic light-emitting diode, an organic light-emitting cell, or an organic light-emitting field-effect transistor.
[0121] In some embodiments, the light-emitting element can be applied to various electronic devices, such as display panels, lighting devices, and light sources.
[0122] In some embodiments, the organic functional layer 103 may be a single layer. In this case, the organic functional layer 103 is a mixture layer, which includes a first compound and a second compound. The first compound is selected from one or more organic compounds as described above, and the second compound is selected from one or more hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting guest materials, light-emitting host materials, and organic dyes.
[0123] When the second compound is selected from one or more of hole injection materials, hole transport materials, electron transport materials, hole blocking materials, light-emitting host materials, and organic dyes, the mass ratio of the first compound to the second compound is 1:99 to 30:70, preferably 1:99 to 10:90.
[0124] When the second compound is a luminescent guest material, the mass ratio of the first compound to the second compound is 99:1 to 70:30, preferably 99:1 to 90:10.
[0125] In some embodiments, the organic functional layer 103 may include multiple layers. When the organic functional layer 103 is multilayered, the organic functional layer 103 includes at least a light-emitting layer 107; preferably, the organic functional layer 103 includes a hole injection layer 104, a hole transport layer 105, a light-emitting layer 107, an electron blocking layer 106, an electron injection layer 109, an electron transport layer 108, or a hole blocking layer.
[0126] In some embodiments, the light-emitting element may be a blue light-emitting element, a green light-emitting element, or a red light-emitting element, and the light-emitting layer 107 may include a host material and a guest material. The guest material may be one or more organic compounds as described above, and the host material may include fused aromatic derivatives or heteroaromatic compounds.
[0127] The light-emitting element has an emission wavelength between 300 and 1000 nm; further, the light-emitting element has an emission wavelength between 350 and 900 nm; and even further, the light-emitting element has an emission wavelength between 400 and 800 nm.
[0128] In some embodiments, the host material includes at least one of anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentane derivatives, phenanthrene compounds, fluoranthene compounds, carbazole derivatives, dibenzofuran derivatives, ladder-type furan compounds, and pyrimidine derivatives.
[0129] In some embodiments, the mass ratio of the host material to the guest material is 99:1 to 70:30, such as 90:10, 85:15, 80:20, 75:25, etc.; preferably 99:1 to 90:10, such as 97:3, 96:4, 95:5, 93:7, 92:8, etc. The guest material is dispersed in the host material, and the mass ratio of the host material to the guest material is 99:1 to 70:30, which helps to suppress the crystallization of the light-emitting layer 107 and suppress the concentration quenching caused by the high concentration of the guest material, thereby improving the luminous efficiency of the light-emitting element.
[0130] In some embodiments, the anode is a hole-injecting electrode, and the anode can inject holes into the organic functional layer 103, such as by injecting holes into the hole injection layer, the hole transport layer, or the light-emitting layer. The anode may include at least one of a conductive metal, a conductive metal oxide, or a conductive polymer. Preferably, the absolute value of the difference between the work function of the anode and the HOMO (Highest Occupied Molecular Orbital) level or valence band level of the light-emitting material in the light-emitting layer, or the p-type semiconductor material in the hole injection layer, hole transport layer, or electron blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. The material of the anode includes, but is not limited to, at least one of Al, Cu, Au, Ag, Mg, Fe, Co, Ni, Mn, Pd, Pt, ITO (Indium Tin Oxide), aluminum-doped zinc oxide (AZO), or other suitable and known anode materials, which can be readily selected and used by those skilled in the art. The anode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc. In some embodiments, the anode can be patterned, for example, patterned ITO conductive substrates are commercially available and can be used to fabricate the light-emitting element of the present invention.
[0131] In some embodiments, the cathode is an electron-injecting electrode, and the cathode can inject electrons into the organic functional layer, such as injecting electrons into the electron injection layer, electron transport layer, or light-emitting layer. The cathode may include at least one of a conductive metal or a conductive metal oxide. Preferably, the absolute value of the difference between the work function of the cathode and the LUMO (Lowest Unoccupied Molecular Orbital) level or conduction band level of the light-emitting material in the light-emitting layer, or the n-type semiconductor material serving as the electron injection layer, electron transport layer, or hole blocking layer, is less than 0.5 eV, preferably less than 0.3 eV, and more preferably less than 0.2 eV. All materials that can be used as cathodes in organic electronic devices may be used as cathode materials for the devices of this invention, including but not limited to at least one of Al, Au, Ag, Ca, Ba, Mg, LiF / Al, MgAg alloy, BaF2 / Al, Cu, Fe, Co, Ni, Mn, Pd, Pt, and ITO. The cathode material can be deposited using any suitable technique, such as suitable physical vapor deposition methods, including radio frequency magnetron sputtering, vacuum thermal evaporation, electron beam (e-beam), etc.
[0132] In some embodiments, the hole injection layer 104 facilitates hole injection from the anode to the light-emitting layer 107, and the hole injection layer 104 includes a hole injection material that can receive holes injected from the positive electrode at low voltage. Preferably, the highest occupied molecular orbital (HOMO) of the hole injection material lies between the work function of the anode material and the HOMO of the functional material of the film layer on the side away from the anode (e.g., the hole transport material of the hole transport layer). The hole injection material includes, but is not limited to, at least one of metalloporphyrins, oligothiophenes, arylamine-based organic materials, hexanitrile hexaazabenzophenanthrene-based organic materials, quinacridone-based organic materials, perylene-based organic materials, anthraquinones, polyaniline-based conductive polymers, and polythiophene-based conductive polymers.
[0133] In some embodiments, the hole transport layer 105 can be used to transport holes to the light-emitting layer 107. The hole transport layer 105 includes a hole transport material that receives holes transported from the anode or the hole injection layer and transfers the holes to the light-emitting layer. The hole transport material is a material with high hole mobility known in the art, and may include, but is not limited to, at least one of arylamine-based organic materials, conductive polymers, and block copolymers having both conjugated and non-conjugated portions.
[0134] In some embodiments, the electron transport layer 108 is used to transport electrons. The electron transport layer 108 includes an electron transport material that receives electrons injected from the negative electrode and transfers the electrons to the light-emitting layer 107. The electron transport material is a material with high electron mobility known in the art, and may include, but is not limited to, at least one of: Al complexes of 8-hydroxyquinoline, complexes containing Alq3, organic radical compounds, hydroxyflavonoid-metal complexes, lithium 8-hydroxyquinoline (LiQ), and benzimidazole-based compounds.
[0135] In some embodiments, the electron injection layer 109 is used for injecting electrons. The electron injection layer 109 includes an electron injection material, which preferably has the ability to transport electrons, has the effect of injecting electrons from the negative electrode, and has an excellent effect of injecting electrons into the light-emitting layer 107 or the light-emitting material. It also has the ability to prevent excitons generated by the light-emitting layer 107 from migrating to the hole injection layer, and also has excellent thin film formation capabilities. The electron injection material includes, but is not limited to, at least one of lithium 8-hydroxyquinoline (LiQ), fluorenone, anthraquinone dimethane, biphenylquinone, thiamethane dioxide, azole, diazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenemethane, anthrone, and their derivatives, metal complex compounds, and nitrogen-containing five-membered ring derivatives.
[0136] In some embodiments, the hole blocking layer is used to block holes from reaching the negative electrode, and can typically be formed under the same conditions as the hole injection layer 104. The hole blocking layer includes a hole blocking material, which includes, but is not limited to, at least one of diazole or triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, etc.
[0137] Please see Figure 1 In some embodiments, the light-emitting element further includes a substrate 110, wherein the first electrode 101, the hole injection layer 104, the hole transport layer 105, the electron blocking layer 106, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially stacked on the substrate 110. See also... Figure 2The first electrode 101, the hole injection layer 104, the hole transport layer 105, the light-emitting layer 107, the electron transport layer 108, the electron injection layer 109, and the second electrode 102 are sequentially stacked on the substrate 110. The substrate 110 can be a transparent substrate or an opaque substrate. When the substrate 110 is a transparent substrate, a transparent light-emitting element can be fabricated. The substrate 110 can be a rigid substrate or a flexible substrate with elasticity. The material of the substrate 110 can include, but is not limited to, plastics, polymers, metals, semiconductor wafers, or glass. Preferably, the substrate 110 includes at least one smooth surface for forming the anode on that surface. More preferably, the surface is free of surface defects. Preferably, the substrate 110 is made of polymer film or plastic, including but not limited to polyethylene terephthalate (PET material) and polyethylene glycol (2,6-naphthalene) (PEN material). The glass transition temperature of the substrate 110 is greater than or equal to 150°C, preferably greater than or equal to 200°C, more preferably greater than or equal to 250°C, and most preferably greater than or equal to 300°C.
[0138] In some embodiments, the light-emitting element may be a solution-based light-emitting element, that is, at least one of the organic functional layers is prepared by a printing method (e.g., inkjet printing).
[0139] In some embodiments, the mixture layer or the light-emitting layer can be formed by a printing or coating process of the composition. Printing or coating processes include inkjet printing, nozzle printing, letterpress printing, screen printing, dip coating, spin coating, knife coating, roller printing, torsional roller printing, offset printing, flexographic printing, rotary printing, spraying, brushing, pad printing, slot-type extrusion coating, etc. Preferably, gravure printing, inkjet printing, and other similar processes are used.
[0140] The composition may be a solution or a suspension, and may include a dispersed phase and a dispersant. The dispersed phase is one or more of the organic compounds described above, and the dispersant is used to disperse the dispersed phase.
[0141] In the composition, the mass fraction of the organic compound as described above can be from 0.01% to 10%, preferably from 0.1% to 15%, more preferably from 0.2% to 5%, and most preferably from 0.25% to 3%.
[0142] Preferably, the Hansen solubility parameter of the dispersant is within the following range: the δd (dispersion force) of the dispersant is between 17.0 and 23.2 MPa. 1 / 2 The preferred range is 18.5–21.0 MPa. 1 / 2The range; δp (polar force) is 0.2–12.5 MPa. 1 / 2 The preferred range is 2.0–6.0 MPa. 1 / 2 The range; δh (hydrogen bond force) is in the range of 0.9–14.2 MPa. 1 / 2 The preferred range is 2.0–6.0 MPa. 1 / 2 The range.
[0143] Preferably, the dispersant has a boiling point greater than or equal to 150°C; more preferably greater than or equal to 180°C; even more preferably greater than or equal to 200°C; more preferably greater than or equal to 250°C; further preferably greater than or equal to 275°C; and most preferably ≥300°C. A boiling point of at least 150°C for the dispersant is beneficial in preventing nozzle clogging of the inkjet printhead during inkjet printing, and a higher boiling point is more conducive to preventing clogging.
[0144] The dispersant may include at least one organic solvent, which can evaporate from the solvent system to form a thin film containing the functional material. The organic solvent may include at least one first organic solvent, which may be selected from aromatic or heteroaromatic compounds. Specifically, the first organic solvent may be selected from p-diisopropylbenzene, pentamene, tetrahydronaphthalene, cyclohexylbenzene, chloronaphthalene, 1,4-dimethylnaphthalene, 3-isopropylbiphenyl, p-methylisopropylbenzene, dipentene, tripentene, pentamethylene, o-diethylbenzene, m-diethylbenzene, p-diethylbenzene, 1,2,3,4-tetramethylbenzene, 1,2,3,5-tetramethylbenzene, 1,2,4,5-tetramethylbenzene, butyric acid, dodecylbenzene, dihexylbenzene, dibutylbenzene, p-diisopropylbenzene, cyclohexylbenzene, benzylbutylbenzene, dimethylnaphthalene, 3-isopropylbenzene... Biphenyl, p-methylisopropylbenzene, 1-methylnaphthalene, 1,2,4-trichlorobenzene, 4,4-difluorodiphenylmethane, 1,2-dimethoxy-4-(1-propenyl)benzene, diphenylmethane, 2-phenylpyridine, 3-phenylpyridine, N-methyldiphenylamine, 4-isopropylbiphenyl, α,α-dichlorodiphenylmethane, 4-(3-phenylpropyl)pyridine, benzyl benzoate, 1,1-bis(3,4-dimethylphenyl)ethane, 2-isopropylnaphthalene, quinoline, isoquinoline, methyl 2-furanate, ethyl 2-furanate, etc.
[0145] The first organic solvent may be selected from aromatic ketone solvents. Specifically, the first organic solvent may be selected from 1-tetrahydronaphthone, 2-tetrahydronaphthone, 2-(phenylepoxy)tetrahydronaphthone, 6-(methoxy)tetrahydronaphthone, acetophenone, phenylacetone, benzophenone, and their derivatives, such as 4-methylacetophenone, 3-methylacetophenone, 2-methylacetophenone, 4-methylphenylacetone, 3-methylphenylacetone, 2-methylphenylacetone, etc.
[0146] The first organic solvent may be selected from aromatic ether solvents. Specifically, the first organic solvent may be selected from 3-phenoxytoluene, butoxybenzene, p-anisaldehyde dimethyl acetal, tetrahydro-2-phenoxy-2H-pyran, 1,2-dimethoxy-4-(1-propenyl)benzene, 1,4-benzodioxane, 1,3-dipropylbenzene, 2,5-dimethoxytoluene, 4-ethylbenzene, 1,3-dipropoxybenzene, 1,2,4-trimethoxybenzene, 4-(1-propenyl)-1,2-dimethoxybenzene, 1,3-dimethoxybenzene, glycidylphenyl ether, dibenzyl ether, 4-tert-butylanisole, trans-p-propenylanisole, 1,2-dimethoxybenzene, 1-methoxynaphthalene, diphenyl ether, 2-phenoxymethyl ether, 2-phenoxytetrahydrofuran, ethyl-2-naphthyl ether, etc.
[0147] The first organic solvent may be selected from aliphatic ketones. Specifically, the first organic solvent may be selected from aliphatic ketones, such as 2-nonanone, 3-nonanone, 5-nonanone, 2-decanone, 2,5-hexanedione, 2,6,8-trimethyl-4-nonanone, frankinc, phorone, isophorone, di-n-pentyl ketone, etc.; or aliphatic ethers, such as pentanyl ether, hexane ether, dioctyl ether, ethylene glycol dibutyl ether, diethylene glycol diethyl ether, diethylene glycol butyl methyl ether, diethylene glycol dibutyl ether, triethylene glycol dimethyl ether, triethylene glycol ethyl methyl ether, triethylene glycol butyl methyl ether, tripropylene glycol dimethyl ether, tetraethylene glycol dimethyl ether, etc.
[0148] The first organic solvent can be selected from organic ester solvents. Specifically, the first solvent can be selected from alkyl octanoate, alkyl sebacate, alkyl stearate, alkyl benzoate, alkyl phenylacetate, alkyl cinnamate, alkyl oxalate, alkyl maleate, alkyl lactone, alkyl oleate, etc. Octyl octanoate, diethyl sebacate, diallyl phthalate, isononyl isononanoate, etc. are particularly preferred.
[0149] The organic solvent may further include a second organic solvent, which may be selected from one or more solvents such as methanol, ethanol, 2-methoxyethanol, dichloromethane, trichloromethane, chlorobenzene, o-dichlorobenzene, tetrahydrofuran, anisole, morpholine, toluene, o-xylene, m-xylene, p-xylene, 1,4-dioxane, acetone, methyl ethyl ketone, 1,2-dichloroethane, 3-phenoxytoluene, 1,1,1-trichloroethane, 1,1,2,2-tetrachloroethane, ethyl acetate, butyl acetate, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, tetrahydronaphthalene, naphthane, and indene.
[0150] In addition to the dispersed phase and the dispersant, the composition may also include one or more components such as surfactants, lubricants, wetting agents, dispersants, hydrophobic agents, adhesives, etc., for adjusting viscosity, film-forming properties, improving adhesion, etc.
[0151] The exemplary preparation methods of the organic compounds provided by the present invention are shown in the following exemplary embodiments 1 to 16.
[0152] Example 1
[0153] Organic compound M1 Synthesis
[0154] The synthetic route for organic compound M1 is as follows:
[0155]
[0156] The specific synthetic steps of organic compound M1 are as follows:
[0157] Synthesis of intermediate M1-3: Under nitrogen atmosphere, intermediate M1-1 (30.8 g, 100 mmol), compound M1-2 (28.1 g, 100 mmol), compound Pd2(dba)3 (2.76 g, 3 mmol), compound tri-tert-butylphosphine (1.2 g, 6 mmol), compound sodium tert-butoxide (18.2 g, 200 mmol) and 250 mL of anhydrous toluene solvent were added to a 500 mL two-necked flask. The mixture was heated to 60 °C and stirred for 6 hours. After cooling to room temperature, the reaction was quenched with water. Most of the solvent was evaporated by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 74%.
[0158] Synthesis of intermediate M1-6: Under nitrogen atmosphere, intermediate M1-4 (19.6 g, 60 mmol), compound M1-5 (17.9 g, 120 mmol), compound Pd2(dba)3 (3.32 g, 3.6 mmol), compound tri-tert-butylphosphine (1.44 g, 7.2 mmol), compound sodium tert-butoxide (11 g, 120 mmol) and 150 mL of anhydrous toluene solvent were added to a 500 mL two-necked flask. The mixture was heated to 70 °C and stirred for 6 hours. After cooling to room temperature, the reaction was quenched with water. Most of the solvent was evaporated by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 62%.
[0159] Synthesis of intermediate M1-8: Following the synthetic method of compound M1-3, compounds M1-7 and M1-6 were used to replace compounds M1-1 and 1-2, respectively, with a yield of 56%.
[0160] Synthesis of intermediate M1-9: Under nitrogen atmosphere, intermediate M1-8 (11.9 g, 20 mmol), compound M1-3 (10.2 g, 20 mmol), compound Pd2(dba)3 (0.92 g, 1 mmol), compound tri-tert-butylphosphine (0.4 g, 2 mmol), compound sodium tert-butoxide (3.64 g, 40 mmol) and 150 mL of anhydrous toluene solvent were added to a 500 mL two-necked flask. The mixture was heated to 90 °C and stirred for 6 hours. After cooling to room temperature, the reaction was quenched with water. Most of the solvent was evaporated by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 65%.
[0161] Synthesis of organic compound M1: Under nitrogen atmosphere, compound M1-9 (10.7 g, 10 mmol) and 80 mL of anhydrous tetrahydrofuran were added to a 250 mL three-necked flask. The temperature was lowered to -30 °C, and 15 mmol of tert-butyllithium solution was slowly added dropwise. After the addition was complete, the reaction was heated to 60 °C and stirred for 2 hours. The reaction was then cooled to -30 °C, and 20 mmol of boron tribromide was added at once. The reaction was allowed to rise naturally to room temperature for 1 hour. 30 mmol of N,N-diisopropylethylamine was added, and the temperature was slowly raised to 100 °C for 3 hours. The reaction was then stopped, cooled to room temperature, and the reaction was quenched with sodium acetate aqueous solution. Most of the solvent was removed by rotary evaporation. The solution was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography after rotary evaporation. The yield was 28%. The atmospheric pressure solid-phase probe mass spectrometry (ASAP-MS) result of organic compound M1 was: MS(ASAP) = 1041.
[0162] Example 2
[0163] Organic compound M2 Synthesis
[0164] The synthetic route for organic compound M2 is as follows:
[0165]
[0166] The specific synthetic steps of organic compound M2 are as follows:
[0167] Synthesis of intermediate M2-3: Following the synthesis method of compound M1-3, compounds M2-1 and M2-2 were substituted for compounds M1-1 and 1-2, respectively, with a yield of 76%.
[0168] Synthesis of intermediate M2-4: Under nitrogen atmosphere, intermediate M1-6 (27.8 g, 60 mmol), compound M2-3 (50.9 g, 120 mmol), compound Pd2(dba)3 (3.32 g, 3.6 mmol), compound tri-tert-butylphosphine (1.44 g, 7.2 mmol), compound sodium tert-butoxide (11 g, 120 mmol) and 150 mL of anhydrous toluene solvent were added to a 500 mL two-necked flask. The mixture was heated to 90 °C and stirred for 6 hours. After cooling to room temperature, the reaction was quenched with water. Most of the solvent was evaporated by rotary evaporation. The mixture was washed three times with water after being dissolved in dichloromethane. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 68%.
[0169] Synthesis of compound M2: Following the synthesis method of compound M1, compound M2-4 was used to replace compound M1-9, with a yield of 25%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M2: MS(ASAP) = 1212.
[0170] Example 3
[0171] Organic compound M3 Synthesis
[0172] The synthetic route for organic compound M3 is as follows:
[0173]
[0174] The specific synthetic steps of organic compound M3 are as follows:
[0175] Synthesis of intermediate M3-3: Under nitrogen atmosphere, compound M3-1 (28.1 g, 100 mmol), NaOH (6 g, 150 mmol), and 150 mL of dimethylformamide were added to a 500 mL two-necked flask and stirred for 1 hour. Iodomethane (15.6 g, 110 mmol) was added all at once, and the mixture was stirred for 4 hours. After the reaction was completed, the reaction solution was poured into 300 mL of pure water, stirred, and filtered to obtain a solid. The solid was purified by recrystallization with a mixture of ethanol and dichloromethane, with a yield of 82%.
[0176] Synthesis of intermediate M3-4: Following the synthesis method of compound M1-3, compounds M3-3 and M2-2 were used to replace compounds M1-1 and 1-2, respectively, with a yield of 72%.
[0177] Synthesis of intermediate M3-6: Following the synthesis method of compound M1-8, compound M3-5 was substituted for compound M1-7, with a yield of 58%.
[0178] Synthesis of intermediate M3-7: Following the synthesis method of compound M1-9, compounds M3-4 and M3-6 were used to replace compounds M1-3 and 1-8, respectively, with a yield of 67%.
[0179] Synthesis of compound M3: Following the synthesis method of compound M1, compound M3-7 was used to replace compound M1-9, with a yield of 27%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M3: MS(ASAP) = 1083.
[0180] Example 4
[0181] Organic compound M4 Synthesis
[0182] The synthetic route for organic compound M4 is as follows:
[0183]
[0184] The specific synthetic steps of organic compound M4 are as follows:
[0185] Synthesis of intermediate M4-2: Following the synthesis method of compound M1-3, compounds M4-1 and M2-2 were substituted for compounds M1-1 and 1-2, respectively, with a yield of 73%.
[0186] Synthesis of intermediate M4-4: Following the synthetic method of compound M1-9, compounds M4-2 and M4-3 were substituted for compounds M1-3 and 1-8, respectively, with a yield of 66%.
[0187] Synthesis of compound M4: Following the synthesis method of compound M1, compound M4-4 was used to replace compound M1-9, with a yield of 24%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M4: MS(ASAP) = 957.
[0188] Example 5
[0189] Organic compound M5 Synthesis
[0190] The synthetic route for organic compound M5 is as follows:
[0191]
[0192] The specific synthetic steps of organic compound M5 are as follows:
[0193] Synthesis of intermediate M5-2: Following the synthesis method of compound M1-3, compound M5-1 was substituted for compound M1-1, with a yield of 75%.
[0194] Synthesis of intermediate M5-3: Following the synthetic method of compound M1-9, compound M5-2 was substituted for compound 1-3, with a yield of 68%.
[0195] Synthesis of compound M5: Following the synthesis method of compound M1, compound M5-3 was used to replace compound M1-9, with a yield of 29%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M5: MS(ASAP) = 1015.
[0196] Example 6
[0197] Organic compound M6 Synthesis
[0198] The synthetic route for organic compound M6 is as follows:
[0199]
[0200] The specific synthetic steps of organic compound M6 are as follows:
[0201] Synthesis of intermediate M6-1: Following the synthetic method of compound M1-9, compounds M5-2 and M4-3 were substituted for compounds M1-3 and 1-8, respectively, with a yield of 64%.
[0202] Synthesis of compound M6: Following the synthesis method of compound M1, compound M6-1 was used to replace compound M1-9, with a yield of 27%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M6: MS(ASAP) = 1029.
[0203] Example 7
[0204] Organic compound M7 Synthesis
[0205] The synthetic route for organic compound M7 is as follows:
[0206]
[0207] The specific synthetic steps of organic compound M7 are as follows:
[0208] Synthesis of intermediate M7-2: Following the synthesis method of compound M1-3, compounds M7-1 and M2-2 were substituted for compounds M1-1 and 1-2, respectively, with a yield of 74%.
[0209] Synthesis of intermediate M7-3: Following the synthetic method of compound M1-9, compounds M7-2 and M3-6 were used to replace compounds M1-3 and 1-8, respectively, with a yield of 65%.
[0210] Synthesis of compound M7: Following the synthesis method of compound M1, compound M7-3 was used to replace compound M1-9, with a yield of 30%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M7: MS(ASAP) = 1070.
[0211] Example 8
[0212] Organic compound M8 Synthesis
[0213] The synthetic route for organic compound M8 is as follows:
[0214]
[0215] The specific synthetic steps of organic compound M8 are as follows:
[0216] Synthesis of intermediate M8-2: Following the synthesis method of compound M1-3, compounds M5-1 and M2-2 were substituted for compounds M1-1 and 1-2, respectively, with a yield of 76%.
[0217] Synthesis of intermediate M8-3: Following the synthesis method of compound M2-4, compound M8-2 was substituted for compound M2-3, with a yield of 70%.
[0218] Synthesis of compound M8: Following the synthesis method of compound M1, compound M8-3 was used to replace compound M1-9, with a yield of 26%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M8: MS(ASAP) = 1160.
[0219] Example 9
[0220] Organic compound M9 Synthesis
[0221] The synthetic route for organic compound M9 is as follows:
[0222]
[0223] The specific synthetic steps of organic compound M9 are as follows:
[0224] Synthesis of intermediate M9-2: Following the synthesis method of compound M1-3, compounds M9-1 and M2-2 were substituted for compounds M1-1 and 1-2, respectively, with a yield of 75%.
[0225] Synthesis of intermediate M9-3: Following the synthetic method of compound M1-9, compounds M9-2 and M3-6 were used to replace compounds M1-3 and 1-8, respectively, with a yield of 66%.
[0226] Synthesis of compound M9: Following the synthesis method of compound M1, compound M9-3 was used to replace compound M1-9, with a yield of 27%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M1: MS(ASAP) = 1086.
[0227] Example 10
[0228] Organic compound M10 Synthesis
[0229] The synthetic route for organic compound M10 is as follows:
[0230]
[0231] The specific synthetic steps of organic compound M10 are as follows:
[0232] Synthesis of intermediate M10-2: Following the synthesis method of compound M1-3, compound M10-1 was substituted for compound M1-1, with a yield of 72%.
[0233] Synthesis of intermediate M10-5: Under nitrogen atmosphere, 40 mL of aqueous solution of compound M10-3 (39.6 g, 100 mmol), compound M10-4 (12.7 g, 100 mmol), tetrakis(triphenylphosphine)palladium (3.3 g, 3 mmol), potassium carbonate (20.6 g, 150 mmol), and 200 mL of toluene were added to a 500 mL three-necked flask. The mixture was heated and stirred at 110 °C for 12 hours. After the reaction was stopped, the mixture was cooled to room temperature, and the filtrate was filtered. Most of the solvent was removed by rotary evaporation. The filtrate was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 70%.
[0234] Synthesis of intermediate M10-6: Following the synthetic method of compound M1-6, compound M10-5 was substituted for compound M1-4, with a yield of 61%.
[0235] Synthesis of intermediate M10-7: Following the synthesis method of compound M1-8, compound M10-6 was substituted for compound M1-6, with a yield of 54%.
[0236] Synthesis of intermediate M10-8: Following the synthesis method of compound M1-9, compounds M10-2 and M10-7 were used to replace compounds M1-3 and M1-8, respectively, with a yield of 63%.
[0237] Synthesis of compound M10: Following the synthesis method of compound M1, compound M10-8 was used to replace compound M1-9, with a yield of 26%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M10: MS(ASAP) = 1055.
[0238] Example 11
[0239] Organic compound M11 Synthesis
[0240] The synthetic route for organic compound M11 is as follows:
[0241]
[0242] The specific synthetic steps of organic compound M11 are as follows:
[0243] Synthesis of intermediate M11-1: Following the synthetic method of compound M1-8, compound M9-2 was substituted for compound M1-7, with a yield of 52%.
[0244] Synthesis of intermediate M11-2: Following the synthesis method of compound M1-9, compounds M8-2 and M11-1 were used to replace compounds M1-3 and 1-8, respectively, with a yield of 62%.
[0245] Synthesis of compound M11: Following the synthesis method of compound M1, compound M11-2 was used to replace compound M1-9, with a yield of 25%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M11: MS(ASAP) = 1176.
[0246] Example 12
[0247] Organic compound M12 Synthesis
[0248] The synthetic route for organic compound M12 is as follows:
[0249]
[0250] The specific synthetic steps of organic compound M12 are as follows:
[0251] Synthesis of intermediate M12-2: Following the synthesis method of compound M1-3, compound M12-1 was substituted for compound M1-1, with a yield of 70%.
[0252] Synthesis of intermediate M12-5: Following the synthesis method of compound M10-5, compounds M12-3 and M12-4 were substituted for compounds M10-4 and 10-3, respectively, with a yield of 66%.
[0253] Synthesis of intermediate M12-7: Under nitrogen atmosphere, compound M12-5 (20.6 g, 60 mmol), compound M12-6 (9 g, 60 mmol), CuI (0.57 g, 3 mmol), potassium carbonate (13.8 g, 100 mmol), and 150 mL of dimethylformamide were added to a 500 mL two-necked flask. The mixture was heated to 110 °C and stirred for 12 hours. After cooling to room temperature, most of the solvent was evaporated by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 62%.
[0254] Synthesis of intermediate M12-8: Under nitrogen atmosphere, intermediate M12-7 (12.4 g, 30 mmol), compound M1-5 (4.5 g, 30 mmol), compound Pd2(dba)3 (1.66 g, 1.8 mmol), compound tri-tert-butylphosphine (0.72 g, 3.6 mmol), compound sodium tert-butoxide (5.5 g, 60 mmol) and 100 mL of anhydrous toluene solvent were added to a 350 mL two-necked flask. The mixture was heated to 90 °C and stirred for 6 hours. After cooling to room temperature, the reaction was quenched with water. Most of the solvent was evaporated by rotary evaporation. The mixture was dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 65%.
[0255] Synthesis of intermediate M12-9: Following the synthetic method of compound M1-9, compounds M12-2 and M12-8 were substituted for compounds M1-3 and 1-8, respectively, with a yield of 64%.
[0256] Synthesis of compound M12: Following the synthesis method of compound M1, compound M12-9 was substituted for compound M1-9, with a yield of 31%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M12: MS(ASAP) = 971.
[0257] Example 13
[0258] Organic compound M13 Synthesis
[0259] The synthetic route for organic compound M13 is as follows:
[0260]
[0261] The specific synthetic steps of organic compound M13 are as follows:
[0262] Synthesis of intermediate M13-2: Following the synthesis method of compound M3-3, compound M13-1 was substituted for compound M3-1, with a yield of 80%.
[0263] Synthesis of intermediate M13-3: Following the synthetic method of compound M1-3, compound M13-2 was substituted for compound M1-1, with a yield of 72%.
[0264] Synthesis of intermediate M13-5: Under nitrogen atmosphere, compound M13-4 (35.2 g, 100 mmol) and 100 mL of anhydrous tetrahydrofuran solvent were added to a 500 mL three-necked flask, stirred and dissolved, cooled to -78 °C, and 100 mmol of n-butyllithium was slowly added dropwise. The reaction was carried out for 2 hours, and 150 mmol of deuterated water was added at once. The reaction solution was allowed to slowly rise to room temperature, and the reaction was continued to be stirred for 4 hours. After the reaction was completed, most of the solvent was evaporated by rotary evaporation, dissolved in dichloromethane and washed three times with water. The organic liquid was collected and purified by column chromatography with silica gel. The yield was 67%.
[0265] Synthesis of intermediate M13-6: Following the synthesis method of compound M12-7, compound M13-5 was substituted for compound M12-5, with a yield of 62%.
[0266] Synthesis of intermediate M13-7: Following the synthesis method of compound M12-8, compound M13-6 was substituted for compound M12-7, with a yield of 66%.
[0267] Synthesis of intermediate M13-8: Following the synthesis method of compound M1-9, compounds M13-3 and M13-7 were substituted for compounds M1-3 and 1-8, respectively, with a yield of 63%.
[0268] Synthesis of compound M13: Following the synthesis method of compound M1, compound M13-8 was used to replace compound M1-9, with a yield of 32%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M13: MS(ASAP) = 841.
[0269] Example 14
[0270] Organic compound M14 Synthesis
[0271] The synthetic route for organic compound M14 is as follows:
[0272]
[0273] The specific synthetic steps of organic compound M14 are as follows:
[0274] Synthesis of intermediate M14-3: Following the synthesis method of compound M12-7, compounds M14-1 and M14-2 were used to replace compounds M12-5 and M12-6, respectively, with a yield of 64%.
[0275] Synthesis of intermediate M14-4: Following the synthesis method of compound M12-8, compound M14-3 was substituted for compound M12-7, with a yield of 64%.
[0276] Synthesis of intermediate M14-5: Following the synthetic method of compound M1-9, compounds M7-2 and M14-4 were used to replace compounds M1-3 and 1-8, respectively, with a yield of 65%.
[0277] Synthesis of compound M14: Following the synthesis method of compound M1, compound M14-5 was substituted for compound M1-9, with a yield of 31%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M14: MS(ASAP) = 938.
[0278] Example 15
[0279] Organic compound M15 Synthesis
[0280] The synthetic route for organic compound M15 is as follows:
[0281]
[0282] The specific synthetic steps of organic compound M15 are as follows:
[0283] Synthesis of intermediate M15-2: Following the synthesis method of compound M1-3, compound M15-1 was substituted for compound M1-1, with a yield of 73%.
[0284] Synthesis of intermediate M15-4: Following the synthesis method of compound M12-7, compound M15-3 was substituted for compound M12-5, with a yield of 65%.
[0285] Synthesis of intermediate M15-6: Following the synthesis method of compound M12-8, compounds M15-4 and M15-5 were substituted for compounds M12-7 and 1-5, respectively, with a yield of 67%.
[0286] Synthesis of intermediate M15-7: Following the synthesis method of compound M1-9, compounds M15-2 and M15-6 were used to replace compounds M1-3 and 1-8, respectively, with a yield of 68%.
[0287] Synthesis of compound M15: Following the synthesis method of compound M1, compound M15-7 was used to replace compound M1-9, with a yield of 33%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M15: MS(ASAP) = 1064.
[0288] Example 16
[0289] Organic compound M16 Synthesis
[0290] The synthetic route for organic compound M16 is as follows:
[0291]
[0292] The specific synthetic steps of organic compound M16 are as follows:
[0293] Synthesis of intermediate M16-2: Following the synthesis method of compound M1-3, compound M16-1 was substituted for compound M1-1, with a yield of 72%.
[0294] Synthesis of intermediate M16-5: Following the synthesis method of compound M12-7, compounds M16-3 and M16-4 were substituted for compounds M12-6 and M12-5, respectively, with a yield of 67%.
[0295] Synthesis of intermediate M16-6: Following the synthesis method of compound M12-8, compound M16-5 was substituted for compound M12-7, with a yield of 62%.
[0296] Synthesis of intermediate M16-7: Following the synthesis method of compound M1-9, compounds M16-2 and M16-6 were used to replace compounds M1-3 and 1-8, respectively, with a yield of 64%.
[0297] Synthesis of compound M16: Following the synthesis method of compound M1, compound M16-7 was used to replace compound M1-9, with a yield of 33%. Atmospheric pressure solid-phase analysis probe mass spectrometry (ASAP-MS) results of organic compound M16: MS(ASAP) = 913.
[0298] An exemplary manufacturing process for the light-emitting element provided by the present invention is shown in the following exemplary embodiment 17.
[0299] Example 17
[0300] In this embodiment, the fabrication steps of the light-emitting element having an anode (ITO) / hole injection layer (40nm) / hole transport layer (100nm) / light-emitting layer (host material: 3% (mass ratio) guest material) (50nm) / electron transport layer (25nm) / cathode (LiQ (1nm) / Al (150nm)) are as follows:
[0301] a. Cleaning of conductive glass substrate: When using it for the first time, it can be cleaned with various solvents, such as chloroform, ketone, and isopropanol, and then treated with ultraviolet ozone plasma.
[0302] b. Following the order of hole injection layer (40nm), hole transport layer (100nm), light-emitting layer (50nm), and electron transport layer (25nm), sequentially apply the layers in a high vacuum (1×10⁻⁶ nm). -6 Film deposition by thermal evaporation at mbar;
[0303] c. Cathode: LiQ (1nm) / Al (150nm) in high vacuum (1×10⁻⁶ nm) -6 It is formed by thermal evaporation in mbar;
[0304] d. Encapsulation: The device is encapsulated in a nitrogen glove box using UV-cured resin.
[0305] In this embodiment, the guest materials are organic compounds M1-M16 to form light-emitting element 1-light-emitting element 16, and the guest material is Ref-1 to form contrast element 1.
[0306] The structural formula of Ref-1 is:
[0307] Of the light-emitting elements 1-16, and the comparison element 1,
[0308] The structural formula of the material of the hole injection layer is:
[0309] The structural formula of the material of the hole transport layer is:
[0310] The structural formula of the host material in the light-emitting layer is:
[0311] The structural formula of the material of the electron transport layer is:
[0312] The structural formula of LiQ is:
[0313] In this embodiment, external quantum efficiency (EQE) and luminous lifetime (T90@1000 nits, which refers to the time it takes for the device under test to decay from 1000 nits to 900 nits) were tested on light-emitting elements 1-16 and comparison element 1. The results are shown in Table 1.
[0314] Table 1: Performance data of light-emitting elements 1-16 and comparison element 1
[0315]
[0316]
[0317] As shown in Table 1, when the external quantum efficiency and luminescence lifetime of the control element 1 are taken as a baseline value 1, the external quantum efficiency of light-emitting elements 1 to 16 are significantly improved, and the luminescence lifetime is also effectively extended. This indicates that the introduction of amine substituents at key sites enhances the resonance effect and steric effect of the organic compound, improves the performance of the guest material, and effectively enhances the luminescence efficiency and luminescence lifetime of the light-emitting elements.
[0318] The light-emitting element disclosed in this invention uses an amine-containing organic compound, which simultaneously contains heterocycles and amine groups, to enhance the resonance effect of the material applied to the light-emitting element, improve the material properties, increase the luminous efficiency of the light-emitting element, and extend the luminous life of the light-emitting element.
[0319] The present invention also discloses a display panel, which includes any of the light-emitting elements described above.
[0320] The display panel further includes an array substrate located on one side of the light-emitting element, and an encapsulation layer located on the side of the light-emitting element away from the array substrate and covering the light-emitting element. The display panel also includes a polarizer layer located on the side of the encapsulation layer away from the light-emitting element, and a cover plate layer located on the side of the polarizer layer away from the light-emitting element. The polarizer layer can be replaced by a color filter layer, which may include multiple color resists and black matrices located on both sides of the color resists.
[0321] The display panel disclosed in this invention uses a light-emitting element made of an organic compound containing amine groups. This organic compound simultaneously contains heterocycles and amine groups, which enhances the resonance effect of the material applied to the light-emitting element, improves the material properties, increases the luminous efficiency of the light-emitting element, and extends the luminous life of the light-emitting element.
[0322] This invention discloses an organic compound, a light-emitting element, and a display panel. The organic compound has a structure as shown in general formula (1): This invention enhances the resonance effect of materials used in light-emitting elements by using an amine-containing organic compound that simultaneously contains heterocycles and amine groups, thereby improving material properties, increasing the luminous efficiency of the light-emitting element, and extending the luminous lifespan of the light-emitting element.
[0323] The organic compound, light-emitting element, and display panel provided in the embodiments of the present invention have been described in detail above. Specific examples have been used to illustrate the principles and implementation methods of the present invention. The description of the above embodiments is only for the purpose of helping to understand the method and core ideas of the present invention. At the same time, for those skilled in the art, there will be changes in the specific implementation methods and application scope based on the ideas of the present invention. Therefore, the content of this specification should not be construed as a limitation of the present invention.
Claims
1. An organic compound, characterized in that, The organic compound is selected from the following compounds: 。 2. A light-emitting element, characterized in that, include: A pair of electrodes, including a first electrode and a second electrode; An organic functional layer located between the first electrode and the second electrode; The material of the organic functional layer includes one or more organic compounds as described in claim 1.
3. The light-emitting element according to claim 2, characterized in that, The organic functional layer includes at least a light-emitting layer, which comprises a host material and a guest material, wherein the guest material is one or more organic compounds as described in claim 1.
4. A display panel, characterized in that, Includes the light-emitting element as described in any one of claims 2 to 3.
Citation Information
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